


Ready

by TheLittleRedWhoCouldWrite



Series: Request Fills [4]
Category: Supernatural
Genre: F/M, First Time, Loss of Virginity, Reader-Insert
Language: English
Status: Completed
Published: 2017-02-12
Updated: 2017-02-12
Packaged: 2018-09-23 22:01:42
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,336
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/9680834
Author URL: https://archiveofourown.org/users/TheLittleRedWhoCouldWrite/pseuds/TheLittleRedWhoCouldWrite
Summary: The reader is a virgin and Sam doesn’t know.





	

You lower the gun and turn to look at Sam questioningly. “How was that?”

“Really good,” he replies, taking the gun. “I think we can call it a day. I think Dean’s making burgers for dinner.”

“I could go for burgers.”

Sam smiles and loops his arm around your waist. He presses a kiss to the top of your head and leads the way back to the main areas of the bunker. “So, this Friday. I’m thinking dinner?”

“Why, are you asking me on a date?” you tease, curling one hand into his plaid over shirt.

“I might just be. Does six sound okay?”

“Six sounds wonderful. Come on, I’m hungry and those burgers smell really good.”

* * *

Friday night finds you and Sam in a small restaurant in Lebanon. It’s been a long time since you’ve had the opportunity to take a night off like this, with the Darkness on the loose. Most of your “dates” have a third wheel- Dean- so dinner with just the two of you is a treat. Sam is a perfect gentleman, right up until he parks the Impala in the garage and you lean across the seat to front kiss him.

Sam grins and pulls you closer. One arm loops around your waist, big hand coming up to cradle the back of your head. You grip the front of his jacket, pressing close to him. His body is huge against yours when he gently pulls you into his lap. His free hand settles in the small of your back, fingers dipping under the waistband of your jeans.

You move your hands up to his shoulders, pulling back. “Sam…”

“What’s wrong?” he asks, gently brushing back your hair.

“Can… can we slow down?” you say nervously, avoiding his gaze.

“Of course,” Sam replies without any hesitation, looking concerned. “Are you alright?”

“Yeah, I’m good. I just want to keep things slow for a while,” you assure him. “Can you… move your hand?”

“My… oh!” he quickly moves his hand up higher on your back. “Better?”

“Much.”

* * *

In all honesty, you wouldn’t mind going further than making out. Sam’s a gorgeous man in every sense of the word. The problem isn’t Sam. It’s you.

The problem is that you’re a virgin in pretty much every sense of the word and you really aren’t looking forward to that conversation. So whenever things start to move into territory outside the make-out zone, you reluctantly pull back. Sam is always gracious. You know he has to be frustrated, but he would never tell you. That’s not how Sam works.

You’re almost grateful when a series of hunts come your way. You and the boys spend a couple weeks living out of motel rooms, long enough to miss the bunker and the privacy it allows.

Dean shuts himself in his room the first chance he gets, leaving you and Sam to entertain yourself. Which, of course, quickly develops into a make-out session on Sam’s bed instead of watching the episode of _Brain Games_ Sam had started.

Your fingers are woven into Sam’s hair when his brush over the hem of your t-shirt. Your whole body stiffens against your will. Sam freezes, pulling back to look at you with concern.

“What’s wrong?” he asks.

“Nothing,” you lie.

You lean in to kiss him again, but he gently cups your face to stop you. “Y/N,” he says softly. “Something’s up. You know you can talk to me about anything, right?”

“Yeah, I know…”

“Then tell me what’s wrong. Please. I’m worried. I know you want to take things slow and I’ll respect your wishes regardless, but I would just like to know why. I need to know where the boundaries are so I don’t accidentally hurt you.”

You could keep lying to him, but you don’t want to do that. You hate lying time Sam, especially when he’s being so thoughtful and is so genuinely concerned for your wellbeing. You tuck your head down against his shoulder and take a deep breath.

“I’m a virgin,” you say, words slurring together until they’re practically indecipherable.

“What was that?” Sam asks, one big hand gently cradling the back of your head. His other arm is solid and secure across the small of your back.

“I’m a virgin,” you repeat, lifting your head a little and forcing yourself to slow down.

Sam is silent for a moment and panic rises up in your chest. It comes to a screeching halt when he nods and says, “Okay. I understand.”

You sit back. “You understand?”

“Yeah. You’re a virgin and because of that, you’re nervous about having sex with me. That’s okay. Everyone is nervous for their first time.” he presses a kiss to your forehead. “Thank you for telling me.”

“You’re not mad that I didn’t tell you?” you ask, shifting nervously on the bed.

“Of course not. That sort of stuff is really personal. Would you have told me if I hadn’t pushed you?”

“Probably not.”

“And that’s okay. I’m glad you trusted me enough to share that with me now.” Sam leans in and kisses you softly. “You set the pace here, sweetheart. We’ll only go as far as you feel comfortable.”

“Can we… kiss some more?” you ask tentatively, hands sliding over his chest the toy with the buttons on the front of his shirt.

He chuckles softly and cups your face in his big hands. You melt into him when he kisses you, letting him pull you into his lap.

* * *

Things get easier after that. Sam is careful, When he feels that he’s pushing a boundary, he backs off and checks in. The regular communication makes being intimate better, because you know he’s paying attention and remembering. Gradually, you move from fully clothed making-out to mostly clothed to mostly unclothed. Together, you learn each other’s bodies. You grow more comfortable with yourself and with Sam touching you. He practically worships your body.

“Sam?” you say one night when the two of your are lying together in Sam’s room, stripped down to your underwear.

“Yes, sweetheart?”

“I want… I want to go all the way. I want to try.”

He lifts up on one elbow and uses his free hand to brush your hair from your face. “Are you sure?”

“I’m sure. Just… go slow.”

“Of course.”

Sam curls his hand behind your neck to lift you up into a kiss. You wrap your arms around his neck. He rolls so you’re straddling his hips, hands falling to your waist. When you’re ready, you guide one of his hands up to the clasp of your bra.

“Ready?” Sam asks, lips brushing against your with each word.

“Uh-huh.”

He undoes the clasp with a skill that can only can be gained through experience. The straps slip down your shoulders and Sam slowly helps you out of them. He drops your bra over the side of the bed, keeping his eyes locked on yours. His hands return to your waist.

“You can touch,” you tell him, sitting up.

You take his hands in yours and lift them to cover your breasts. He carefully brushes his thumbs over the skin, catching your nipples as he does so. You bite your lip.

“Do you like that?” he asks.

You nod and he grins. He lifts up so he can wrap his mouth around one nipple, drawing a soft gasp from you. He sucks and nibbles until you’re arching into him. Your hips are grinding against his, the bulge of his erection clear even through two layers of fabric. The realization of just how well-endowed Sam is hits you then.

“Oh,” you breathe, hands flying to his shoulders. “ _Sam_.”

“What’s wrong?” he asks, lifting his head.

You rock your hips experimentally, feeling him twitch against you. Despite the doubts running through your head, your pussy is slick enough to dampen the fabric of your panties.

“You’re really big,” you murmur, almost embarrassed.

“If you change your mind, that’s okay,” Sam assures you, shifting for he’s sitting up fully with you in his lap. “I understand.”

“No, I want to do this,” you say firmly, tightening your grip on his shoulders.

“Okay. If you’re sure.”

You kiss him, weaving your fingers into his hair. He loops his arms around your waist and pulls you tight against him, bare chests pressed together. The sensation of skin-on-skin in such a manner is something new and extraordinary.

Sam lifts you up, turning to lay you on your back on the mattress. His body blankets yours. “I’m going to take my boxers off,” he tells you. “And then your panties. Okay?”

“Okay,” you say.

He gets off the bed, standing by the side. When his hands go to his waistband, so do yours. You glance up to meet his gaze and he nods. Biting your lip, you slowly pull his boxers down.

Sam’s cock springs free, long and hard and curving up towards his stomach. You’ve seen men naked before- you’re a virgin, not a prude- but you’ve never thought of a cock as beautiful before. This is Sam’s cock, though, and Sam is beautiful.

You wrap a tentative hand around him, stroking slowly. Sam moans, eyes falling shut, and you can’t help a grin. Knowing he feels good and that you’re the one making him feel good is a huge turn-on.

“Fuck, Y/N,” he says, dropping his hand to your wrist. “If you keep that up, this’ll be over before it’s started.”

You reluctantly let go, laying back on the bed. Sam takes a deep breath.

“Let me grab a condom,” he says as he moves around the bed to his dresser. You watch him dig through the top drawer and pull out a couple foil packets. He rejoins you on the bed, tossing them onto the nightstand. Sam looms over you. “Can I take your panties off?”

You nod, lifting your hips so he can work the soft fabric out from under you. The cool air hits your slick skin and you shiver.

“Beautiful,” Sam whispers, fingers sliding over the skin of your thighs. “I want to taste you? Can I?”

“Okay,” you say, spreading your legs a little.

Sam positions himself between your legs, spreading your thighs with his huge hands. You blush a little, feeling exposed when his hungry gaze lands on your pussy. He bends down, practically laying on his stomach, and rests his cheek against the top of your thigh. He blows softly and you gasp, feeling your pussy clench. Smiling, Sam dives in. His tongue works quickly between your folds, his mouth traveling up and down to figure out exactly how to make you scream. You grab at his hair and cry out when he moans, the vibrations enough to send you over the edge. Apparently Sam has a hair-pulling kink. You’ll have to remember that.

He sits back, grinning. “How was that?”

“Fuck,” you breath, gazing down at him. “That was… wow.”

“How are you feeling?” he asks, rising up until he’s level with your again.

“Really good.”

“Think you’re ready for more?”

“Yeah, I am.”

Sam kisses you, one hand sliding down to cup your pussy. His middle finger slips between your folds and rubs gently over your entrance. He moves to circle your clit, making you grind up into his hand. He quickly works you through another orgasm. When you’ve come down from the high, he starts to push his finger inside. You stiffen and he freezes.

“Shit, sorry, I should have warned you,” he says, pulling his hand away.

You grab his wrist. “No, don’t stop. I was just surprised.”

“You’re sure?” Sam asks, looking at you intently.

“Yes, I’m sure. I want this.”

“Alright. Just tell me if anything hurts. It shouldn’t, but I want you to communicate what you’re feeling. Okay?”

You nod and let go of his wrist. He pushes his finger into you again and you force yourself to stay relaxed, furrowing your brow a little at the new sensation.

“It’s good,” you say before he can ask. “Just… new.”

Sam carefully works his finger in and out, twisting and curling it to stimulate your inner walls until you’re loose enough to fit a second finger. The process continues You’re surprised to find yourself rolling your hips onto four of his long fingers. He’s palm rubs over your clit with each movement of his hand.

“Sam, I need you,” you manage, fingers clawing at his shoulders. “ _Please_.”

“Shhh, I’ve got you,” he soothes, gently withdrawing his fingers and twisting to grab a condom from the nightstand. He rolls it on quickly and fits himself between yours thighs. You bite your lip as he lines up and begins to press in.

“Oh, fuck,” you gasp, head falling back against the pillow. “Fuck, _Sam._ ”

“Everything okay?” he inquires, lifting your thighs around his hips.

“ _Don’t stop_.”

Sam chuckles. “Yes, ma’am.”

It feels like forever before his hips are pressed against yours. The stretch is a lot and you know you’re going to be aching tomorrow, but at the same time it feels amazing. Sam leans over you, watching your expressions.

“I’m going to start moving,” he says. “Remember, tell me if anything feels wrong.”

“I will.”

He starts slow, gradually working his way up to a steady rhythm that has you dancing on the edge. If there’s one thing Sam’s good at, it’s sex. He lets you hold onto him, not complaining when your fingernails dig into his upper back. You’re probably leaving marks, but he doesn’t seem to mind.

Your third orgasm comes on gradually, leaving your a trembling mess beneath Sam. He follows you over the edge, head falling forward to press against yours. When he’s recovered, he carefully pulls out. He quickly disposes of the condom and stretches out beside you.

“How do you feel?” he questions, curling one arm around your waist.

“We’re definitely doing that again,” you reply.

Sam’s face lights up. “Really?”

You twist to kiss him. “Really.”


End file.
